In previous posts, I’ve discussed the grander goal(s) of my monthly challenges — developing a self-success framework and upgrading my operating system in doing so. This post will deal with the break down of the “how” question.

Each month, starting last month, continuing through this one and through the end of the year (minus a July reflection month), I’ll be taking on three monthly challenges. These are broken into three categories that mean a lot to me and my life (writing, health, and a happy lifestyle), but that’s not here nor there. In fact, the challenges themselves are not the end game. Though I’m working hard to pick challenges that I’ve wanted to do, take on, or have avoided in the past — the real end goal is the learning that comes from taking these on month after month.

Last month, for instance, I took on a squat challenge. I failed, BUT….

Already there have been learnings about myself:

I have a long way to go on squatting, but writing is easier. I do better with gratitude at night as my day is winding down and I’m reflecting than I do in the morning as my day is just beginning. I’m pretty good at sitting in my meditation — once I can get it going. Also, bachelor parties tend to kill daily habits — though I suppose that was to be assumed.

What’s certainly been one important learning: habits are important. Getting into a daily habit helps ensure these things get done.

But there’s also just been real learnings in how I can develop my framework:

Attach To-Do’s to Habits

This was a piece of advice given to me by a friend (I believe funneled through another friend). If you already have habits — say brushing your teeth — attach something else onto it to help make that a habit too. So, if for instance, I need to do my L-sits for the day, I may do so before I can brush my teeth. If I know I’m going to have to shower, I’ll write my journal entry before going in there. Not after. I tried that. All that does is delay what you need to do and open up the possibility of forgetting. Do it before. Then go into your habit — since you know that’s going to happen anyway.

Use the “Power” Framework

I’ve also used a reward system for my work on these challenges. For instance, right now I’m dying to go watch the next episode of The Jinx, but I won’t do it until I’ve written this post. That’s helped me stay align with my challenges. Rewards are part of the pattern that Charles Duhigg laid out in his book The Power of Habit as the kind of closing aspect to forming a habit. If you can reward yourself with this action, you’ll further your desire to habitualize, mostly unconsciously. So I’ve tried to use that to my advantage.

New Actions Come with Consequences

For instance, this month I’m doing an V-sit (or L-sit) challenge where I hoist myself up on my arms and hold my bodyweight up with my arms & core. The goal is doing this 5 minutes a day and it’s quite difficult. At first I had to break this up into 9 or 10 sessions (about 30 seconds each). I can now do it in about 7 sessions (6 is my record) of nearly a minute each, and sometimes over. It’s been great — my core has never felt stronger. But I’ve attached this onto my habit of being clean, namely showering and brushing my teeth, and those have often come at the end of my day. The consequence from this, in general, is some tightness in my wrists and my shoulders/upper back. Since I’m often doing this at the end of my day, I’m probably not taking the wind down time I should and I’ve noticed the tightness lingering. I haven’t slept as well as I usually do and I think that’s due to some of that upper back tightness disturbing my laying posture. So even though I’m doing well in the challenge (so far 21 days of 23), there are some side effects I hadn’t considered — in both the challenge itself and the habitualizaition.